3-amino-5-fluoro-1H-indole-2-carboxylic acid, ethyl ester | 317840-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-amino-5-fluoro-1H-indole-2-carboxylic acid, ethyl ester
• 英文别名: ethyl 3-amino-5-fluoro-1H-indole-2-carboxylate
• CAS: 317840-95-2
• 化学式: C₁₁H₁₁FN₂O₂
• mdl: MFCD00753454
• 分子量: 222.219
• InChiKey: WXAMYHISCJCWJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-amino-5-fluoro-1H-indole-2-carboxylic acid, ethyl ester 在 溶剂黄146 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 2-(4-Fluoro-10-oxo-14-thia-8,11,16-triazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(9),2(7),3,5,15-pentaen-8-yl)acetic acid
  参考文献：
  名称：

  Overcoming fluconazole resistance in Candida albicans clinical isolates with tetracyclic indoles

  摘要：

  Continuing efforts to discover novel means of combating fluconazole resistance in Candida albicans have identified an indole derivative that sensitizes strains demonstrating resistance to fluconazole. This tetracycle (3, ML229) does not appear to act through established Hsp90 or calcineurin pathways to chemosensitize C. albicans, as determined in Saccharomyces cerevisiae models, and may be a useful probe to uncover alternative resistance pathways. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.035
• 作为产物：
  描述：

  5-氟吲哚-2-甲酸乙酯 在 palladium on activated charcoal 、 氢气 、 硝酸 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 3-amino-5-fluoro-1H-indole-2-carboxylic acid, ethyl ester
  参考文献：
  名称：

  [EN] TPK AGONIST AND METHOD FOR TREATING NEURODEGENERATIVE DISEASES USING SAME
  [FR] AGONISTE DE TPK ET PROCÉDÉ DE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES L'UTILISANT
  [ZH] TPK激动剂及使用其治疗神经退行性疾病的方法

  摘要：

  本公开属于生物医药领域，并具体涉及预防或治疗神经退行性疾病或者减轻神经退行性疾病的症状的方法，其包括向需要其的个体给药预防或治疗有效量的硫胺素焦磷酸激酶(TPK)激动剂。

  公开号：

  WO2024012554A1

文献信息

• INTERLEUKIN-4 GENE EXPRESSION INHIBITORS
  申请人：ALKAN Sefik S.

  公开号：US20080132481A1

  公开（公告）日：2008-06-05

  This invention discloses and claims a class of indole and benzo(b)thiophene derivatives for use in treating allergy, asthma, rhinitis, dermatitis, B-cell lymphomas, tumors and diseases associated with bacterial, rhinovirus or respiratory syncytial virus (RSV) infections. The compounds of this invention are defined by the Formula (I): wherein X, Y, Z, R 1 , R 2 and R 3 are as defined in the specification; or a pharmaceutically acceptable salt thereof. In preferred embodiments of this invention it is also disclosed and claimed that the compounds of this invention are capable of modulating T helper (Th) cells, Th1/Th2, and thereby capable of inhibiting the transcription of interleukin-4 (IL-4) message, IL-4 release or IL-4 production.

  本发明揭示和声明了一类用于治疗过敏、哮喘、鼻炎、皮炎、B细胞淋巴瘤、肿瘤以及与细菌、鼻病毒或呼吸道合胞病毒（RSV）感染相关的疾病的吲哚和苯并(b)噻吩衍生物。本发明的化合物由公式（I）定义：其中X、Y、Z、R1、R2和R3如规范中所定义；或其药学上可接受的盐。在本发明的优选实施例中，还揭示和声明本发明的化合物能够调节T辅助（Th）细胞，Th1 / Th2，并能够抑制白细胞介素-4（IL-4）信息的转录、IL-4的释放或IL-4的产生。
• 3-substituted amino-1H-indole-2-carboxylic acid and 3-substituted amino-benzo[B]thiophene-2carboxylic acid derivatives as interleukin-4 gene expression inhibitors
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP1834947A2

  公开（公告）日：2007-09-19

  This invention discloses and claims a new class of indole derivatives for use in treating allergy, asthma, rhinitis, dermatitis, B-cell lymphomas, tumors and diseases associated with bacterial, rhinovirus or respiratory syncytial virus (RSV) infections. It has now been found that the compounds of this invention are capable of modulating T helper (Th) cells, Thl/Th2, and thereby capable of inhibiting the transcription of interleukin-4 (IL-4) message, IL-4 release or IL-4 production.

  本发明公开了一类新的吲哚衍生物，用于治疗过敏、哮喘、鼻炎、皮炎、B 细胞淋巴瘤、肿瘤以及与细菌、鼻病毒或呼吸道合胞病毒（RSV）感染有关的疾病。现已发现，本发明的化合物能够调节 T 辅助（Th）细胞 Thl/Th2，从而能够抑制白细胞介素-4（IL-4）信息的转录、IL-4 的释放或 IL-4 的产生。
• 3-(PYRIDINYL-AMINO)-1H-INDOLE-2-CARBOXYLIC ACID DERIVATIVES AS INTERLEUKIN-4 GENE EXPRESSION INHIBITORS
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP1501796B1

  公开（公告）日：2007-05-09
• US7169925B2
  申请人：——

  公开号：US7169925B2

  公开（公告）日：2007-01-30
• Overcoming fluconazole resistance in Candida albicans clinical isolates with tetracyclic indoles
  作者：Willmen Youngsaye、Chris Dockendorff、Benjamin Vincent、Cathy L. Hartland、Joshua A. Bittker、Sivaraman Dandapani、Michelle Palmer、Luke Whitesell、Susan Lindquist、Stuart L. Schreiber、Benito Munoz

  DOI：10.1016/j.bmcl.2012.02.035

  日期：2012.5

  Continuing efforts to discover novel means of combating fluconazole resistance in Candida albicans have identified an indole derivative that sensitizes strains demonstrating resistance to fluconazole. This tetracycle (3, ML229) does not appear to act through established Hsp90 or calcineurin pathways to chemosensitize C. albicans, as determined in Saccharomyces cerevisiae models, and may be a useful probe to uncover alternative resistance pathways. (C) 2012 Elsevier Ltd. All rights reserved.